Hell Buddies
by cjalabrat4
Summary: Before Dean's deal was up Bobby told him about a friend who got pulled down under a few years back and asked Dean to pass along a message. He never thought he'd see that person let alone become friends with him but when Castiel shows up to drag him out he let's him know they both go or they both stay. DISCLAIMER: I don't own anything but some of the plot. Sequel to come
1. Chapter 1

**Chapter One**

 _"Hey Dean."_

 _The young hunter looked up from his bottle of beer and gazed at his adoptive father._

 _"Yeah Bobby?" He replied in a whisper. They were in the living room at Singer Salvage and Sammy was asleep right up stairs. Maybe his little brother had the right idea, it was nearly midnight._

 _"If we don't find a solution to this," Bobby seemed to hesitate before taking a deep breath and continuing. "A while back a friend of mine got pulled down where you're headed. I don't know if he's still down there or even a bit of what he used to be but if you see him I was hopin' you could do me a favor."_

 _"Anything Bobby, you know that," Dean said as he realized where this was going._

 _"His name is Harry and if he still has them his eyes are as green as an emerald. If you see him down there please tell him that we don't blame him and know he did what he had to. He'll know what I mean I just need him to know that."_

 _"Of course Bobby," Dean said before taking a sip of his beer. And that was that._

* * *

That one conversation he had with Bobby a few weeks before everything went up in smoke stuck with Dean the most once he woke up on the rack. It wasn't until a decade in though that he realized what Bobby meant by as green as an emerald. Alistair was due to walk in at any moment and Dean was trying to prepare himself the pain that would surely happen when he did. But when he heard the demon enter, he heard someone else thrown in before hand.

"Welcome to my newest project. Something tells me this will finally break you Harry," hissed the demon into the ear of a small, waif-like, human.

Dean looked at the pair in surprise when he heard that name, the name that kept repeating itself in his mental ear for the past ten years. He thought it could be a coincident until the young human looked up at him met his gaze with the greenest eyes he'd ever seen. He didn't have time to say or even think anything though before Alistair threw Harry to the side and approached the curious hunter.

"Let's begin shall we," Alistair snarled as he began what he did every day. Which was torture the defenseless hunter. Today he decided to relish the pain that would practically ooze from the hunter and skin the poor bastard.

As the evil mother fucker began clawing at his abdomen Dean just knew he was gonna get skinned, again.

* * *

After what felt like years, Alistair finally left Dean to his pain. The hunter was panting in short gasps of pain and wished he could just close his eyes but his lids were one of the first things the demon took. He had forgot all about the other person in the room until he heard footsteps moving closer.

"I apologize for what I'm about to do because it will hurt, but only briefly," the smaller man said with a british lilt. Dean wanted to ask what the hell he meant or tell him not to come anywhere near him but then his whole body started to burn. He wanted to scream but found his throat was to sore. The pain didn't last as long as what Alistair did to him and in comparison wasn't as bad but Dean hadn't saw it coming and they made it all the more worse.

After what was probably half an hour the pain faded to a tingling sensation and then that too faded after another hour. It took Dean a moment to open his eyes and another to realized he could actually close them and had been completely healed. That usually didn't happen until a few hours after Alistair left.

Dean looked around for Harry and noticed him about to leave.

"Wait," Dean said in a raspy voice. "If you're the Harry a friend of mine told me about I have a message for you," He continued when he held the gaze of those green eyes.

"And who is this friend?"

"His name is Bobby, Bobby Singer."

Harry gasped in surprise before walking back to the bound hunter.

"You know Bobby? How is he? Is he still hunting?"

"Yes, he's good, and sometimes. He told me to tell you that they don't blame you and you did what you had to do, whatever that means." Harry nodded his head before sitting down in front of the hunter.

"Well now this is a very welcome surprise. I feel at a loss though, you know my name but I don't know yours."

"Dean, Dean Winchester."

"Nice to meet you Winchester. I guess I'm stuck here until they realize watching you get tortured isn't going to break me so we might as well get to know each other."

"Why aren't you on a rack somewhere if they want to break you?"

"They tried that for the first century but realized I have a high pain tolerance."

"Dude, how long have you been down here?"

"What year was it when your deal was up?"

"2008."

"Well then. I have been down here for going on a decade topside. Which is about 1200 years down here."

* * *

 _ **A/N: It's pretty short but the chapters will most likely grow. Let me know what ya'll think in reviews. :D**_


	2. Chapter 2

**Chapter Two**

"Oh that was just brutal mate," Harry said to a groaning Dean.

"Hardy har har, can you just do your mojo and heal me already?"

"I don't know this is a good look for you. Now you really will be talking out your arse." Harry laughed as he moved to help his friend. It had been thirty years since they met and yet neither of them had cracked. Dean was still on the rack and Harry was still forced to watch. Sometimes Harry wished that he had faked it a little better in the beginning but for some reason no matter what a demon did to him he couldn't feel the pain. He had talked with Dean about it and they were both sure it was because he wasn't meant to be down here.

* * *

Don't misunderstand there was a deal made and it did involve Harry's soul. It just wasn't made by Harry. Harry didn't even know about it until the dogs came for him. When he had told Dean that the hunter had cussed up a storm. Especially when Harry told him what Alistair had said about the Ministry of Magic making the deal.

This wasn't the demons problem though. Their job was to break the souls sent to them and nothing more. So they tried other ways to break Harry. They thought making him watch Dean would be the final straw. What they didn't expect was Harry and Dean to bond. Bobby asking Dean to pass along that message was the best thing to happen to both wizard and hunter.

* * *

"Ugh, never again am I going to Hell. I'm firing my travel agent soon as I'm out of here."

"Really Dean, Sarcasm does not look good on you at all."

"Shut up Harry. Be glad you can't feel pain like this."

Harry just rolled his eyes.

* * *

 _Ten Years Later_

After forty years of being in close quarters with each other it would be hard to spot any differences between the hunter and wizard. Sure they looked different but both had brown hair and green eyes. They both frowned the same and smiled the same and ever laughed in the same bitter way. Their voices had also evened out to give Harry a more american drawl and Dean's had a little bit of a British lilt to it. It wasn't noticeable to the two men or even to the demon who tortured Dean but if even topside heard them talk they would be surprised at the difference.

* * *

"I CAN'T TAKE IT ANY MORE!" Dean yelled with a hoarse voice.

"Does this mean your answer has changed Deany boy?"

"Ye-"

"Dean!" Came another voice. "Fight this."

"Sammy?"

"Yes Dean, please for me?"

"For Sam- for Sammy," the hunter mumbled incoherently not noticing an anger Alistair dragging Harry away. He was already passed out from the pain and would be until Harry dragged his way back to the safety that was the hunter's little cubicle of hell to heal himself in peace.

* * *

"SAMMY!" Dean woke up screaming.

"Dean, It's okay!"

"Harry? I heard Sammy Harry! We gotta save him he can't be down here."

"You were just dreaming Dean. Passing out from intense pain will do that to you."

"You sure," the still drowsy hunter asked.

"I'm sure Dean," the wizard whispered to the dosing hunter.

'What he doesn't know can't hurt him,' Harry thought to himself as he went back to regrowing his legs. Glad that Alistair had dragged far enough so Dean couldn't hear his surprised yelp of pain when they had a hell dog rip both legs off. It was only a pinch of pain but it was pain none the less. That meant something bad was happening, Harry just knew it.

* * *

Harry had made it all the way to the last little toe when a white light filled the room. He jerked his head up just as Dean jerked awake with a painful gasp.

"No! NO, NO, NO! If you take me you gotta bring Harry!"

Said wizard gasped. It was an angel! It could sense the etheral beauty and power coming from the white light that had formed into the shape of a human but with wings.

"We have plans for you Dean Winchester not for the wizard." The words had a song like beauty to it even though they were delivered telepathically.

"HE ISN'T SUPPOSED TO BE DOWN HERE TO BEGIN WITH!" Dean yelled in righteous anger. The angel like form turned to Harry with a new attitude then and Harry could sense it thinking.

"Very well," came the telepathic words again. "I will bring the savior also. Be warned wizard you face many a problem when you return to earth."

Harry couldn't help but snort. Like he didn't know that already. Before he could reply though the angel's light burned brighter and spread out to the wizard and hunter until even closing their eyes wouldn't help.

'What am I getting into now'

'How am I gonna explain this to Sammy' ****

* * *

 _ **A/N: Sorry for the wait and the short chapter. I just got to looking at my stories for the first time in weeks and got hit by the writin' bug. Hope ya'll enjoy**_


	3. Chapter 3

Chapter Three

 _ **A/N: Canon variation at bottom**_

* * *

 **London, England**

 **Gringots Bank**

The first thing Harry saw when he opened his eyes was blue ones looking back at him.

"AH!" Harry screamed as he tried to jerk away and ended up hitting his head.

"Finally, you are awake. The goblins believed we would have to shock you with a spell soon," came a voice belonging to the blue eyed man, now standing a few feet away.

"Goblins? Wha-"

"You were brought here ten years ago Lord Potter. Upon the finding of your body ancient law was put into place do to a centuries old prophesy," came the deep, accented voice of a goblin. Harry turned around to notice Griphook. He was much older looking but Griphook all the same.

"Prophesy? Don't tell me there's another one!"

"I'm afraid there is Harry. But please follow me to my office so we can talk in comfort." The goblin pressed his hand against the wall and as the door rolled open that's when Harry had been in one of the lowest vaults in the bank. He went to follow his old friend only to be stopped by a hand on his arm.

"Lord Potter, I must leave you now to make sure Dean get's to his family safely. It has been foresaw he will run into trouble and I don't want him to be hurt."

"You're the one who pulled us out! What are you?" Harry asked with suspicion.

"I am Castiel, an Angel of the Lord." With that the self proclaimed Angel disappeared with only the sound of fluttering wings in his wake. Harry just shook his head hard to clear it and ran after Griphook.

"Now Harry. I believe the beginning would be the best place to start," Griphook said as they settled in front and behind his desk.

Harry snorted and quirked an eyebrow.

"Over 600 years ago there was a famed prophetess who was never wrong. She was revered by the King and kept within the castle where her every need was met to keep her happy. One night at dinner she turned towards the king and said this prophesy:

 _After surviving once_

 _He will survive again_

 _A decade in Hell_

 _Numb only to pain_

 _He will rise again_

 _A changed man this wizard will fight_

 _to save the world from brothers_

 _with brothers_

 _wizard and hunter unite_

 _against the apocalypse they will triumph_

 _true love abound and peace at last._

"Holy Merlin what have I gotten into."

Griphook just chuckled grimly before tapping a gem on his desk with a long nail. A younger goblin walked in with a box in his hands and a chest floating behind him. He sat them on the desk in front of Harry and walked back out.

"The small box has a list of everything you've inherited when you became of age and everything you were willed from people who respected you and your family. The chest is all of your property we were able to obtain before looters got to it."

Harry reached for the smaller box and lifted the lid. Inside was a list of properties, money, heirlooms, and books from over one hundred families not including the Pottters of the Blacks.

"You now own the title of Lord of 60 families have 100+ seats on the Wizengamot and your vaults could make the Malfoys cry and be jealous."

Harry snorted and opened his mouth to say something. He was interrupted by the flutter of wings coming from behind him. Castiel stood there in his coat and suit with a blank expression.

"Dean Winchester will meet up with his brother in Kansas tomorrow afternoon. You will meet him there."

"If you are leaving the country Lord Potter, a lot of paperwork needs to be filled out."

"Well let's get started then." Castiel disappeared again as another goblin entered with a large stack of papers.

 _The Next Afternoon_

"Well that seems all of it," Harry said as he put the last bit of clothing into his discreetly extended shoulder bag.

"Be safe My Lord," Griphook said with a bow "and remember what I said about demons. You will be able to sense them now and a silent AK will end them completely without harming their host."

"That's awesome Griphook," Harry said as he grabbed the portkey that would take him to the motel the Winchesters were. He felt the usual pulling sensation before he landed in a parking lot a few spots down from a black impala... Right in front of a demon in a young woman's body. Without thinking he grabbed her shoulder before she could bolt, 'Avada Kadavra.' With a single thought the girl fell into his arms and a black cloud flew out of her mouth before burning up from the inside out. The girl was fine so Harry left her in the main office and headed for the room the Impala was parked outside of. He walked up to the door and banged on it a few times. All noise from inside stopped and the door was yanked open by a tall lanky guy with messy, just had sex, hair.

"Did you know a demon just walked out of here? Don't worry I got rid of her for you," Harry said with a smug smirk which widened into a full out grin when the man at the door's jaw dropped along with Dean and another, older man behind him...

* * *

 _ **A/N: So PLOT TWIST and a cliffy. The next chapter will be out soon because I can not shake this bug. Hope Ya'll enjoy and please review.**_


	4. Chapter 4

**Chapter Four**

"Bobby!" Harry said before anyone could react. "I didn't know you'd be here."

Before Sam could react the stranger at the room's door lunged forward and hugged Bobby around the waist. The old hunter looked shocked for a moment before hugging the tiny man tight. Sam looked like he was about to say something but Dean just shook his head. After a few minutes the two men separated and looked at the brothers.

"Knew you were a trouble magnet like me D but a demon? Really."

"About that what do you mean a demon just came out of here. The only person in here with Sammy was a hooker," Dean said with a confused crinkle to his forehead.

"About my height, brown hair, tank top and jeans?" Harry asked. When Dean and Bobby both nodded he nodded even more sure of himself, "Yep a demon."

"How do you know that?" Came an angry voice from the other side of the room. All three turned to see Sam standing there with his arms crossed and glaring at Harry."

"Well apparently spending nearly 1,500 years in Hell gave me the ability to since the filth that breeds there," Harry said with a raised eyebrow and the totally unwarranted anger coming from the tall hunter in waves.

"So what, you've got a knife that sent her back to hell?"

"Nope, simple AK had a black cloud pouring out threw the mouth and imploding. It was very beautiful."

"Why you little-"

"Sammy! What the hell is your problem! You should be thanking Harry for killing that bitch before she could come back and try to finish you off."

"You don't understand Dean," Sam said has he tried to wrestle out of his brother's arms and jump the little wizard who had been pushed behind Bobby as soon as Sam lunged.

"Then you better talk fast Sam because something ain't right."

"I-"

"They were together," Came a flat sounding voice from behind Harry.

"Castiel! I didn't know you'd show up yet," Harry said with a smile. He went towards the angel but was pulled back into a broad chest.

"Dean! What is wrong with you, don't you recognize him?"

"It is expected Lord Potter,"

"Harry, please."

"Harry, I did not show myself to Dean as I did to you. Pulling his soul back into his body took a lot of power and I was unable to keep this form and it would have been unsafe for him to see me in my true form. I was going to wait until you told him about me but sensed an aggressive presence near you both and came to offer assistance."

"It's okay Castiel, it's just Sam. From what you just said I think he's just upset I killed his lover."

"Who the hell is this guy! How did he get in here past all the sigils?"

Harry stepped away from Dean and turned towards the hunters to see they all hand their guns in hand but had them lowered.

"Guys this is Castiel, he's an angel of the lord and was the one who pulled me and Dean out of hell." Sam and Bobby looked unsure but Dean nodded and put his gun in the back of his pants.

"Makes sense and your voice is the one I heard. While we're introducing people why don't you do the same Harry?"

"Wait a minute, I want proof that he's really an angel," Bobby said. Without Harry or Dean asking Castiel took a step forward and unfurled his wings. They couldn't see them fully but the shadows of two beautiful, black wings expanded across the room walls.

"Believe him now?" Dean asked as the other two hunters picked their jaws up off the floor. They nodded as the wings faded back out of existence.

"Now, it's story time for Harry," Dean said has he gestured towards the beds and chairs. Harry sighed and sat down in one of the chairs and watched as the hunters sat around him.

"Well I guess the short version should do for now and please no questions until the end or we'll never finish." Receiving nods from everyone he sighed and looked down at his hands as he started his story.

"Before I start you should know that I am a natural born wizard. No demon deal involved just a magic core. I was a part of a prophesy to defeat a Dark Lord who was at war with the rest of the Natural Born Wizards and the Ministry that ruled our society decided that me, a 17 yr old boy, was not doing all I could to defeat him and decided to take action. They summoned a demon and said that in return for defeating our Dark Lord the demons could have my soul as payment. The demons decided to take the deal and next thing I knew I was on a wrack down in the hell. That was in 1998 and before you say anything it wasn't a decade down there it was more like 1,200 years."

Seeing that Harry was wrapped up in some pretty bad memories Dean picked up the story.

"When I woke up on a wrack down there a demon immediately started torturing me, after he was done another demon came in dragging this tiny little thing of a soul and left us alone. Apparently because Harry wasn't supposed to be down there in the first place he couldn't feel pain. So the demons tried to break him by making him watch others be tortured then have to heal them. After he healed me that first time I noticed his eyes and automatically thought about what you had told me Bobby," He said with a nod towards the older man. "I asked him if he was the Harry that my friend Bobby told me about and I passed along the message. After that Harry stayed in my little corner of hell and kept me from going crazy and breaking. Now 40 years later and here we are." Dean never took his eyes off of Harry so he didn't notice the look of guilt that passed over Sam's face but soon turned to his brother to change the subject.

"So how long were you sleeping with that demon? Did you know she was a demon? If you did why didn't you waste her ass?"

"I- uh-," Sam stuttered before looking away from his brother. "She said she could help me defeat Lilith and I wanted revenge. She told me all I had to do was anything she told me and not ask questions. I, uh, think she fed me her blood last night," Sam trailed off in shame. Dean looked like he was about to say something but Castiel finally stepped forward.

"She did not lie to you Samuel. She fed you her blood to enhance the effects of the demon blood already in your system from Azazel so you would be able to kill Lilith with only a thought. That would be detrimental to everything though Samuel. Fore Lilith is the last key in a series of locks that if 60 were broken then Lucifer would be released from his cage in hell."

* * *

 _ **A/N: So I'm gonna leave it here because he seems like a good spot and has to be the longest chapter I've ever typed so enjoy please review what you think and if you have any idea, suggestions, or corrections if I got something wrong.**_


	5. Chapter 5

**Chapter Five**

Previously...

"Killing Lilith would have been the final seal to break Lucifer our of his cage in Hell"

* * *

Everyone looked at Castiel in shock.

"No way," Sam said in shock before Dean slapped his shoulder with a grin.

"Oh! Little Sammy got played."

Sam glared at his older brother and then Harry and Bobby when they snorted in laughter.

"At least tell us the sex was good," Harry said through his gasps of laughter. Sam just blushed a dark pink.

They all enjoyed a good laugh before getting back to the serious part.

"Well good thing she's not coming back," Harry said with a stiff nod.

"So we just avoided the apocalypse?" Dean asked.

"Not yet," Castiel said somberly. "The first seal was broken when 'a righteous man shed blood in Hell.'"

Every one was silent but Harry frowned.

"But Dean didn't break." This caused Castiel to jerk his head towards the wizard and also frown.

"I was ordered to rescue Dean Winchester from Hell because the first Seal had broke and Heaven needed him to fight for them."

"Well Dean isn't the righteous man that broke. He was being tortured right up until you grabbed us."

Before Castiel could say anything else the sound of ruffling wings filled the room and another angel showed up.

"That is enough talk about something above you Castiel," came a deep voice but before the new comer could grab the young angel Harry jumped forward. The wizard grabbed the strangers wrists before he could touch his friend.

"Hold up there big guy," Harry growled as he silently bound the angel from leaving. "If it's above Castiel maybe you can give us the answers we need."

"I'll say nothing to you _mud-monkey_ ," the man snapped in disgust. All three hunters behind them nearly stood up to defend their newest partner in hunting but the short man just laughed coldly.

"You think that's the worst I've been called," he whispered harshly. "If you don't want to give us answers I have a way to make you talk. I don't know if it works on _your kind,_ but no time better than now to find out."

With that he stepped away from the snarling angel to reach into the bag on his back. He shoved his hand into the biggest opening of the backpack and everyone in the room hear some clinking before the hand was removed and revealed to be holding a stoppered bottle.

"I figured the goblins would put some in here," Harry mumbled before getting back into the angel's personal space as the rest of the people in the room watched in curiosity.

"Do you know what this is?" Without waiting for an answer he pulled out the cork and yanked the mans neck back causing him to gasp in surprise and pain. Harry reached up and poured about a third of the vial into the open mouth.

"Harry?" Dean finally asked in confusion. "What is that stuff?"

"That is truth serum, it has another name but it's really long and I never remember it. Anyway, this is how we're going to get our answers."

"How?" Sam asked with a frown.

"Easy, ask him any question." Everyone turned to the restrained angel in the room and saw his eyes had took on a glazed look.

"Alright," Dean said. "Why did Heaven want me brought out of Hell?"

"Michael ordered everything, Father left centuries ago and Michael is now bored. He has decided to start the apocalypse early by secretly suggesting everything Azazel ever did including pushing that soldier to kill you brother. He wanted you sent to Hell to break the first seal so he and his trusted angels could begin breaking the rest. He had also threatened a demon named Ruby to encourage your brother need for revenge on Lilith and after the first 65 seal were broke she was supposed to lead him to a church where Lilith's blood would open a doorway straight to Lucifer's Cage. Sam and Dean Winchester play the biggest part because they are Lucifer and Michael's vessels respectively. In the end Michael would defeat Lucifer so Paradise could reign. No matter the loss of human life." By the end of it the angel wasn't even talking to Dean anymore just reciting what sounded like his orders given to him by Michael. The others in the room couldn't help but be surprised.

"But Dean didn't break. He never tortured anyone. What will Michael do now since the first seal wasn't broke?"

"He does not think his plan was a bust. He has already given his approval to break the rest of the seals."

"But it won't lead to anything. Will he be able to successfully break the rest of the seals?"

"I do-" Before he could continue another angel showed up.

"Zachariah!" Someone boomed. "Why have you not brought me that ignorant Castiel to be punished!"

"Because he's to busy spilling his, I mean, your secrets Michael," Harry said with a snarl. Michael looked around the room to see three hunters and a wizard glaring at him, his top crony looking high, and Castiel frowning at him.

"What has he told you?"

"Nothing much, you planned everything from Azazel feeding Sam demon's blood as a baby all the way to planning on breaking all the seals because you got bored while Daddy was away," Dean said with a shrug as he continued to glare at the archangel. Michael looked unsure of this development before snarling at everyone and disappearing from the room.

"Well this ain't gonna turn out good," Bobby said with a frown. The other's nodded in agreement.

"What do we do with him," Sam asked as he gestured toward Zachariah.

"We could zap him to Antarctica," Dean suggested. Harry smiled at his best friend before shaking his head.

"Or I could wipe his memory of ever working with Michael in the first place then send him back to Heaven so Castiel has at least one ally up there."

"Let's go with Harry's plan," Sam said with a look at his brother. Dean pouted but nodded in agreement. After getting nods from everyone else, even Castiel, Harry grabbed both sides of Zachariah's head and delved into the angel's mind. He met some resistance but was soon wiping all of his memories going back a quarter of a century. Once he was finished he took a step back and released the angel to see him shake his head in confusion.

"Thank you for your help Zachariah," Harry said with a smile. The angel looked up and realized he didn't know where he was.

"Wha-?"

"Castiel was just explaining how you helped him grab me and Dean from Hell before the first seal could be broke and we're really grateful for that, right Dean?" Harry said while shooting a look at said hunter.

"Yeah man, it's pretty awesome that you did that for us. What with Michael wanting to wait so he could jumpstart the apocalypse early," Dean said understanding the look Harry gave him.

"He did that?" Zachariah asked in shock.

"Yes Zachariah, now we must leave. We have many angels to speak to about Michael's wrongdoings and we must spread the word that the first seal was not broke as Michael hoped," Castiel said, speaking for the first time since Zachariah appeared, and grabbed his brother before they both disappeared.

The humans were silent for a moment before Harry flopped down on one of the beds.

"That was emotional," the wizard said as Dean flopped down beside him.

"What do we do now?" Sam asked.

"We sleep," Dean and Harry said in unison. They would of said something about the shocked looks on Sam and Bobby's faces but they were already asleep.

"Well I'm not tired, you?" Bobby said as he turned to Sam. The younger man shook his head.

"I am hungry though."

"Then let's go find that diner at the edge of town. I could go for something fried."

With that Sam and Bobby left the motel room after leaving a note for the sleeping men. None of them knew what would happen next but they did know that they should appreciate the quiet before the storm as much as possible.

* * *

 _ **A/N: So this was almost a two-shot but I decided not to. I honestly have no clue where this is going or when I'll update again so hope ya'll enjoy and don't forget to REVIEW! 3**_


End file.
